


How Is It We Haven’t Met?

by CeliPuff



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Bottom Castiel/Top Dean Winchester, Castiel is Not Innocent (Supernatural), Castiel/Dean Winchester One Shot, Dean Winchester Has a Crush on Castiel, F/F, Happy Ending, M/M, One Night Stands, Openly Gay Castiel (Supernatural), Openly Gay Dean Winchester, Shameless Smut, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2019-11-20
Updated: 2019-11-20
Packaged: 2021-02-13 17:08:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,329
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21497557
Author URL: https://archiveofourown.org/users/CeliPuff/pseuds/CeliPuff
Summary: Charlie made sure to keep Cas and Dean apart but her birthday has them both under the same roof. Will they respect her wishes and keep it in their pants or will their undeniable chemistry find them in Charlie’s bathroom?
Relationships: Castiel/Dean Winchester, Charlie Bradbury/Jo Harvelle
Comments: 18
Kudos: 142
Collections: Destiel Smash Fest





	How Is It We Haven’t Met?

“Charlie who is _that?_” It takes Charlie a moment to spot who Dean means in the crowd. Her parties are always packed but this year, you can hardly hear the person next to you.

“Oh, Cas? You haven’t met Cas?” She asks, knowing the answer. Dean shakes his head, staring at the man intently. “Yeah, and _this_ is why!” Charlie rolls her eyes, slapping his arm. “No hooking up with him, Dean!”

Dean starts to walk towards this mysterious _Cas_. “What? Charles I can’t hear you. Talk later.”

She reaches for him but his shirt slips through her fingers. “Dammit Winchester!”

Dean heard her but that doesn’t mean he will listen. He’s heard his circle of friends talk about a Cas before. They all have nice things to say about him so he must not be a bad guy, not that it mattered. He was fucking hot as hell and Dean understood why Charlie kept him hidden. _Selfish ass lesbian. I should have kept Jo hidden!_

Charlie was just mad she had to stop hanging out with Michael because he and Dean had a bad breakup. She made Dean promise not to sleep with anymore friends of hers but _come on, this dude has to be a free pass_.

Dean was close enough to hear his laugh and holy shit was his voice deep. Just before he reached Cas, Charlie was pulling his ear, dragging him away. “Dammit Charles!”

Cas didn’t notice Dean until Charlie was pulling his ear. “Who is that??” Cas asked Benny, pointing his beer towards Dean.

“The one in trouble with Charlie? Dean? You don’t know Dean, Cher?” Benny laughed, knowing Charlie must have did that on purpose. He met Cas over a year ago.

“No, I haven’t had the pleasure.” Cas drank his beer, watching Charlie and Dean argue through the glass sliding door. “That won’t do.” Cas decided to say fuck it and go meet this _Dean_.

Benny watched him walk away, “Jo where’s the popcorn? This is going to be entertaining.” He sat back with his beer as Jo moved to sit with him and watch.

“Oh, shit Charlie is going to be pissed.” She laughed, “Five bucks they fuck in the bathroom tonight.” Jo held out her hand.

“Hell no. We all know that _is_ happening tonight the bet should be how _long_ it takes. Five bucks it happens before midnight.” He gripped her hand and shook.

“Fine. I say before 11.” Jo shook back with a grin.

Benny checked the time, “No faith in our Dean keeping it in his pants huh? It’s almost 10 now.”

“I don’t have faith in either of them. I’ve seen Cas with a few beers in him. He disappears with someone almost as much as Dean.” They laughed, watching the scene as Cas reached Charlie and Dean. “Why are our gay boys so slutty?” Jo shook her head with a smile.

Dean stopped talking abruptly causing Charlie to turn around. With a sigh, she threw her arms in the air, “Cas, Dean. Dean, Cas. Enjoy.” She walked away with an eye roll.

“Hey Cas. How is it we haven’t met?” Dean turned the charm up to the next level, pretending he wasn’t thrown off by Cas’ intense blue eyes.

“Hello Dean. I was coming to ask _you_ the same thing. Is it just me or has Charlie kept us apart on purpose?” Cas tilted his head making Dean smile.

“She definitely did. She doesn’t think I can keep it in my pants.” Dean leaned his bottle towards Cas’ and Cas clinked them together before leaning in closer.

“I hope you don’t.” Cas smiled and took a drink making Dean silently curse himself for being such a good friend.

“Well, I sort of promised her I wouldn’t hook up with you _tonight_, she specifically mentioned her bathroom being off limits… so, let’s hang out until midnight and then meet at my Impala.” Dean wiggled his eyebrows and took a drink.

Cas laughed, “Impala huh?” He took a step forward, feeling their friends eyes on them. “Are you trying to impress me?” The glint in Cas’ eyes made Dean’s cock twitch. Both men suddenly doubted they could wait until midnight.

They decided to go back inside after about twenty minutes of talking and getting to know each other. “If we don’t go inside soon I’m going to kiss you.” Dean shrugged as if he couldn’t help it.

Cas laughed, “I guess we can’t have that, it is only,” he checked his phone. “10:25.” Cas pretended to pout before leading the way inside.

Dean couldn’t help but smile, _that was cute._ Dean took the opportunity to check out Cas’ perfect ass and had to ball his fist to keep from reaching out and grabbing the forbidden fruit.

They shocked everyone when they sat on the couch and didn’t rush to the bathroom. Jo was suddenly nervous she would lose the bet, “What’s up guys?” She gave Dean a confused look to which he returned a heavily exaggerated confused look.

Cas looked over when Dean laughed at Jo’s scowl. “What’s up? You mean in the last half hour? Nothing much. What’s up with you, _Jo?_” Cas said with light sarcasm, tilting his head at her innocently.

“Cut the crap. Why are you guys here and not blowing each other in the bathroom?” Benny choked on his beer at Jo’s brazen question and Charlie slapped her arm.

Cas and Dean shared a knowing look before bursting out laughing. Charlie frowned, “What is _this?_” She pointed accusingly at them both, eyes narrowed.

“What Charles? You told us not to fuck around. If I knew we would be given the third degree for doing exactly what _you_ wanted regardless, then I wouldn’t have. Cas, how’s that bathroom sounding?” Dean raised his eyebrows and took a drink of his beer.

Before Cas can answer Charlie spoke up, “No! Stay, you’re right. I’ll shut up about it, let’s all play a game.”

After forty minutes of _Never Have I Ever,_ everyone was pretty drunk. “Charlie, you act like _I’m_ such a slut but look at _your_ drink! You are just as fucked up as us.” Charlie would have blushed at Cas’ comment if she wasn’t so drunk.

“Fuck you, Cas. You _are_ a slut. You too Dean don’t laugh!” Charlie flipped them both off, smiling.

Dean held his hands up, “Woah! I’m sober compared to you two.” Dean pointed at Charlie and Cas.

“That’s because you’ve been taking little _bitch_ drinks all night Dean, but all three of you have drank to almost every question.” Jo never hesitated to call anyone on their shit.

“Little bitch drinks?” Dean challenged just before slamming the rest of his drink down. “Your turn asshat!”

Jo flipped him off while shooting her drink too. “I’m staying the night so I can get as drunk as I want.”

“Guess I’m staying too then. Cas, you staying?” Dean offered Cas a mischievous smile.

“How could I say no?” Cas leaned closer again, not caring who was watching.

“You’re both tops ya know? So, maybe think about that before it gets awkward.” Charlie’s last ditch effort to keep them apart had Cas and Dean staring intently at each other, both were smiling.

Dean barked a laugh, “You really thought that would stop us?” He turned back to Cas, “I’ll bottom for you sexy.” He winked.

Cas shook his head with a grin, “And I’d bottom for you anyday handsome.” He attempted to wink back, except he doesn’t wink well and Dean found himself swooning over everything Cas did.

“Fuck it! I’m just the right amount of drunk to not care anymore. Have fun _sluts_.” Charlie finished her drink and turned to flirt with Jo. Benny laughed and walked to the kitchen to talk to some other friends, not wanting to be a fifth wheel.

Suddenly, Cas and Dean were as alone they could be at a crowded party.

Dean turned to face Cas, watching his perfect lips form a smile. “It seems Charlie doesn’t care anymore.” Cas spoke before Dean could and leaned in.

Dean didn’t respond in words, he grabbed Cas’ shirt and pulled him into a kiss. Dean moaned as Cas parted his lips, allowing his tongue entry. The empty beer bottle slipped from Cas’ grip as he climbed onto Dean’s lap, deepening the kiss.

Charlie couldn’t help but smile, neither of them had ever acted so forward with their hookups but maybe keeping them apart had helped their desire for one another? It _was_ getting a little out of hand though, “Okay boys, get a room, just not my room.” She stood up and went to say goodbye to some guests just as they pulled apart.

Cas went to climb off Dean’s lap but he held him there by his hips. “Wait... Cas, give me a minute.” Cas laughed, looking down at the boner Dean was sporting.

“You're not the only one who can’t walk yet Dean.” Cas’ voice was deeper than it had been before the kiss, not helping Dean’s arousal in the slightest.

After a moment or two, Cas slid from Dean’s lap and turned to walk down the hall, not checking to see if Dean was following.

Dean watched him go, licking his lips as he stood to follow. “Dean, wait.” Dean sighed as Charlie walked up.

“I thought you said it was okay Chuckles. No take backsies.” He pointed a finger at her, scowling.

“No. I’m not. It’s just…” she paused and took a breath, causing Dean’s annoyance to slip away. She obviously felt strongly about this. “Look, I know you both. I kept you apart because you guys would be fucking perfect together. And not just some hookup, actually _together_. But if you hookup and never give it that chance you could both miss out on something amazing. I’m not trying to be a boner killer okay? Just don’t walk out of here tonight with just another notch on your bedpost Dean. Try to at least be friends okay?”

Dean pulled her into a hug. “Charlie I actually really like the guy, there is no way at the end of this that I don’t want to be his friend. Hell, if you didn’t say it was okay to hookup I would have asked him on a date.” Dean blushed and Charlie’s eyes widened.

“What! I take it back, it’s not okay.” Her words held no conviction.

“Too late now. I’ve had a taste and I won't be able to hold back now. But we’ll see where the night goes.” Dean smiled and ruffled her hair.

“Dammit!” She slapped his hand away. “Cas is in the last room to the right, he always sleeps in there when he stays over.” She rolled her eyes as she turned away to hide her smile.

Dean felt suddenly nervous. _Why?_ What was it about _this_ guy that had Dean freaking Winchester nervous? Pushing those thoughts aside he knocked on the door.

Cas had closed the door behind him so he could have a moment to gain his composure, Dean was too good to be true. Cas wanted him in every possible way, the images caused the blood to rush to his cock as Dean knocked on the door.

Cas opened it with a smile, he had already changed into some comfy sweatpants and Dean could see his semi hard erection through the fabric. “Hello Dean.” Cas’ voice sent a chill up Dean’s spine causing him to swallow before he drooled. “I wasn’t sure if Charlie would let you come.” Cas challenged and walked towards the bed to lay back with his hands behind his head.

_Challenge accepted._ Dean walked through the threshold and closed the door, locking it for good measure. “Did you really doubt me?” Dean asked as he walked closer to the bed. His dick waking more with each step closer to the man before him.

Dean didn’t want there to be a moment of awkwardness with Cas. As he approached the bed he decided he would just go for it and kiss Cas again but before he got the chance Cas was grabbing his shirt and pulling him on top of him, their mouths clashing together.

Cas moaned when Dean’s tongue entered and Dean moaned as Cas rolled his hips upwards, his hard erection rubbing on Dean’s. Dean pulled back breathlessly, staring into Cas’ beautiful lust blown cerulean eyes. “Fuck.” Dean whispered as he began kissing and sucking on Cas’ neck.

“Fuck.” Cas whispered back, rolling his hips into Dean again. “Fuck me Dean.”

Dean pulled back again, his green eyes wide. “Really? You sure? Charlie said-”

“Are we really talking about Charlie right now? Or are you going to fuck me into this mattress?” Cas bit his lip, grinding into Dean impatiently.

Dean smiled at him thinking of how beautiful he looked as he writhed beneath him. Dean has never wanted to top _and_ bottom so bad at the same time. He teased Cas, licking and sucking his bottom lip. “I’m going to fuck you into the mattress Cas.” Dean grinned as Cas moaned and squeezed his ass. “But you’re going to hold off and return that favor when I’m done. Got it sweetheart?” Cas nodded enthusiastically, licking his lips.

Their mouths crashed together heatedly, Cas pulled back to shove Dean’s shirt over his head as Dean nearly ripped Cas’ shirt off of him.

Neither of them wanted to stop kissing, it was as if their tongues were made to dance together.

Dean finally pulled back to kiss down Cas’ body. Smiling when he noticed Cas’ rock hard erection was painfully tenting his sweatpants. Dean looked up to stare into Cas’ hooded eyes as he freed Cas’ throbbing member.

“This all for me?” Dean teased, slightly surprised by Cas’ size. Cas nodded again and bit his lip in that way that drove Dean crazy already, causing Dean to slide Cas into his mouth ungracefully.

A shiver ran up Cas’ spine, “Shit. Shit. Fuck.” Cas repeated profanities like a mantra, unable to form other words with Dean’s perfect mouth around his cock.

Dean brought him to the edge, watching Cas the entire time, needing to know what made him tick. As soon as Cas’ hips shuttered, Dean pulled off and kissed his way back up Cas. “Not yet handsome.” Dean’s voice was rough from the blowjob. Cas shoved at Dean’s pants, moaning loudly when their dicks rubbed together for the first time without any barriers.

Dean teased them both for a moment before lowering himself again, this time neglecting Cas’ cock and going straight for his hole. Cas’ squirming was driving Dean wild, he was loving how responsive Cas was to his every touch. His own neglected cock was leaking profusely as he opened Cas up with his tongue. Cas reached under the pillow and threw the bottle of lube down to Dean. “More.” Cas whispered breathlessly.

Dean smiled as he popped the cap on the lube, generously coating his fingers before slowly entering one. Cas gripped the sheets, cursing under his breath. Dean did a pretty good job with his mouth but he didn’t want to hurt Cas at all, especially since Cas was predominantly a top. “More.” Cas whispered again, this time less patient.

Dean huffed a laugh, “You’re bratty huh?” Dean shoved a second finger inside, making Cas hiss. “See? You need to be patient.” Dean kept his fingers still, kissing Cas’ thigh affectionately until he felt Cas relax around him. As he moved in and out he waited to add the third finger until Cas was pushing back into his hand. Once Dean felt Cas was open and ready he slid his fingers out and sat up on his knees, touching his erection for the first time as he lubed himself up. Cas’ hair stuck up in every direction as he bit his lip again, still moving down towards Dean impatiently.

“Dean?” Cas’ voice was thick and deep with arousal. Dean looked into his eyes, Cas stared back for a moment before speaking again, “Dean. Fuck me.”

How could Dean deny him? His voice shook adorably with desperation. Cas had never wanted to be fucked so bad in his life. Any other time he tried bottom was for a boyfriend, and it wasn’t great. Dean lined up, their eyes locked on one another while he slid inside, pausing a couple times to give Cas the time to stretch around him. Cas felt so full when Dean bottomed out. “Fuck Cas so tight.” He leaned down to kiss him, slower this time but still just as passionately.

Cas began to grind into Dean, asking for more with his body. When Dean slid out and back in slowly Cas moaned his name into his ear making Dean worry he wouldn’t last long._ Fuck it_. Dean started his pace, fucking Cas into the mattress just as he asked him to. It wasn’t long before both men felt their orgasms bursting at the seams. “Cas I’m gonna…” Unable to finish his sentence, Dean released into Cas with a groan, filling him up even though he originally planned on pulling out.

Dean gripped the base if Cas’ cock to hold off his orgasm. Shushing him as he complained. “Your turn big boy.” Dean nipped at Cas’ earlobe as he pulled out of Cas.

Cas flipped them before Dean realized what was happening. “I’m not going to last long handsome. That was the best fuck I’ve ever had.” Cas lubed up his fingers and slowly slid one into Dean.

Dean tensed at the intrusion but relished at how long Cas’ fingers were when he brushed it along his prostate with ease. Dean loved being top, but he was no stranger to bottom. It had just been awhile since he _wanted_ to be fucked.

Cas worked him open, both of them impatient by the time he finished. “Cas.” Dean grabbed Cas’ chin to look into his eyes. “Fuck me.”

Cas shivered, “Fuck, you’re so perfect.” Cas lined up and slid inside, both of them moaning loudly. “Oh my god Dean. This ass is heaven.” Cas sucked at Dean’s neck while he adjusted, waiting for Dean to give him the _okay to move_ hip roll bottoms always gave.

Once Dean pushed back into Cas, he began to move. His eyes shut tightly as his orgasm built quickly. Cas was upset he wouldn’t last long, he wanted to stay inside Dean’s perfect ass forever.

“Fuck, Dean I’m close.” Cas whispered breathlessly.

“Come inside me Cas.” Dean gripped Cas’ ass as he spilled into Dean with a whimper.

Both of them laid there, not wanting to move.

“Can I take you to dinner this week?” Dean asked before realizing what he was saying.

Cas pulled out of Dean and laid next to him, staring at him intently. “Um. Yeah.” He asked unsure if Dean meant it or if he just really enjoyed the sex. “You want to stay in here tonight? Maybe have a quickie in the morning?” Cas asked with a smile.

Unable to fight the grin, Dean nodded and pulled Cas into a kiss.

**********

They both woke up sore and opted for quick blowjobs instead. Cas swallowed Dean’s load just as Charlie knocked on the door. “Breakfast sluts!” Dean laughed as he slid on his clothes from the night before.

Just as he laid a hand on the doorknob he turned back to Cas, watching him slide on a t shirt, messing up his bed head even more. Dean couldn’t believe they spent the _whole _night together and they even cuddled, which goes against all the _one night stand_ rules but neither of them cared anymore. This was already something more than a one night stand.

Dean walked back and lifted Cas’ chin up for a chaste kiss. “I meant what I said last night, about dinner.”

Cas grinned, staring into Dean’s beautiful green eyes. “Good.”


End file.
